Ethanol → HCID 67663000, compound

HRID 1455896Notes

Reaction equation

HRID 1455896 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH:22]=[CH:23][C:24]([O:26]C)=[O:25])=[CH:16]2)=[O:11].C(O)C.[OH-].[Na+]>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH:22]=[CH:23][C:24]([OH:26])=[O:25])=[CH:16]2)=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67664036HCID 67664036, compound

Product 1

HCID 67663000HCID 67663000, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22 (60 mg, 0.167 mmol) was dissolved in DMF (1.5 mL) and ethanol (3 mL) was added. 3N NaOH solution (1.5 mL) was added and the reaction mixture was stirred overnight. The solvent was removed and water (10 mL) was added. The solution was neutralized using 20% HCl. The resulting precipitate was filtered and washed with water. 53 mg (92% yield) of yellow solid 23 was obtained. mp: 268° C. (dec). 1H NMR (DMSO-d6, ppm): 12.27 (brs, 1 H, COOH), 11.53 (s, 1 H, NH), 10.38 (s, 1 H, NH), 8.07-7.35 (m, 9 H, Ar--H, CH=CH), 6.88 (s, 1 H, Ar--H), 6.48-6.44 (d, 1 H, J=16.2 Hz, CH=CH). Anal. (C20H14N2O4 0.4H2O), C, H, N.

Workup

  1. customThe solvent was removed
  2. additionwater (10 mL) was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-af158a03fb9a4963811083926cfab80b
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

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